Title: South Side Cottages from CA $564 | Expedia.ca [South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides) ![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search South Side Cottage Rentals from CA $564 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side cottages ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121340000/121330200/121330192/ee4be839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121340000/121330200/121330192/df9330f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121340000/121330200/121330192/7db98038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121340000/121330200/121330192/f9a49026.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Forest Park [](https://www.expedia.ca/Chicago-Hotels-Classic-Forest-Park-Foursquare-1-Mi-To-Blue-Line.h121330192.Hotel-Information) CA $216 CA $564 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Chicago-Hotels-Classic-Forest-Park-Foursquare-1-Mi-To-Blue-Line.h121330192.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-09&endDate=2026-01-10®ionId=553248635074842823&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cottages [](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=COTTAGE) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=VILLA) Condos [](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=CONDO) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=VACATION_HOME) Residences [](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=RESIDENCE) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Cottages.d553248635074842823-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Cottages.d553248635074842823-aaCottages.Travel-Guide-Accommodation) ## Top South Side Hotel Reviews ![Saratoga Motel By Capital O Near Midway Airport Chicago IL](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3451h2304x0y0-39d39828_y.jpg) ### Saratoga Motel By Capital O Near Midway Airport Chicago IL 10/10 Excellent "Great hosts" [](https://expedia.ca/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17_y.jpg) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG 10/10 Excellent "The broom was clean and everything was pleasant. The staff was very professional and friendly. " [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ![SpringHill Suites by Marriott Chicago Chinatown](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg) ### SpringHill Suites by Marriott Chicago Chinatown 10/10 Excellent "Everything was wonderful! From the welcoming feeling when we walked in the door with the bright ambiance and the pleasant smell. They have nice & helpful front desk staff, along with convenient parking . Rooms were spacious, clean and the bed was so comfortable. We were sad to have missed out on the breakfast because we slept in but we had heard it was very good." [](https://expedia.ca/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information) ![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg) ### Hyatt Place Chicago-South/University Medical Center 10/10 Excellent "My grandson and I stayed one night after my husband’s surgery at the University of Chicago Hospital. We had a wonderful stay. The room was spotless, comfortable, and the staff was very helpful. " [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "Excellent " [](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "What a gem of a hotel! Perfect for our overnight stay in Chicago. All was immaculately clean and so well appointed. Very nice staff, too! 5 Stars from us" [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Best Western Inn & Suites - Midway Airport](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg) ### Best Western Inn & Suites - Midway Airport 10/10 Excellent "Surprisingly very nice!! " [](https://expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ![Sophy Hyde Park](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7_y.jpg) ### Sophy Hyde Park 10/10 Excellent "This is a beautiful hotel - so aesthetic and very clean. The customer service was great, too. Will absolutely stay here again. " [](https://expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) ![Mccormick Place Guest House](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/b6c2dad6_y.jpg) ### Mccormick Place Guest House 10/10 Excellent "Awesome. The view was sweet. And very clean. Recommend it " [](https://expedia.ca/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.Hotel-Information) ## Find out more about South Side ## South Side Cottages information | Number of reviews | | | ----------------- | ---------- | | Accommodation | 0 Cottages | | Lowest Price | CA $564 | | Highest Price | CA $564 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Cheap Hotels in Bronzeville ](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Cheap-Hotels.0-n6132245-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Bronzeville ](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Family-Hotel.0-n6132245-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bronzeville ](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Luxury-Hotel.0-n6132245-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Bronzeville Hotels ](https://www.expedia.ca/Bronzeville-Chicago-Hotels.0-n6132245-0.Travel-Guide-Filter-Hotels) - [Canaryville Hotels ](https://www.expedia.ca/Canaryville-Chicago-Hotels.0-n6132307-0.Travel-Guide-Filter-Hotels) - 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